Jeremy has pointed out that 95.5 can cross sell with 93.9 and 103.5 due to targeting similiar female demos. This is/was working for them since they flipped in 2015.
There are some more things to keep in mind however.
The first is Chicago is a very diverse market, it is very hard to maintain 2 full signal country stations here. The second is that when iHeart started 95.5, they did a good job of going after US 99.5 and put a big dent in the young white female demo.
Fast forward almost 3 years to now. US 99.5 rebranded back to US 99, dumped the golds and fired some long standing hosts, replacing them with hosts like S&R in the mornings. This was a huge risk for them, but, it's working right now.
US 99 has managed to stem the tide and slowly gain back or grow that same young female demo that was defecting to BIG 95.5. A big part of 95.5's success at the time was it was new, was commercial free and they were playing the most popular hits, more often.
Now the stations are virtually the same musically, the "Oh Wow" factor of 95.5 has faded and US 99 has rebounded and is now safe again. A year ago that was not the case. 95.5 is not out of the race or doing terribly. They have however lost ground to US 99 and will not likely put the money or effort into the station they did before.
Back to the point, they only have one competitor in the market now, if they flipped to Alternative they would be the 3rd in the market(counting XRT).
They flipped a Detroit station to ALT 106.7 Monday night. This station was Classic Rock until about a year ago. It was changed to an Adult Hits/Jack type format and ratings kept dropping.
This flip to Alternative may have been sped up to beat Entercom to the punch, but, I think this was being planned already anyways.
They are Detroit's only real alternative station right now. They do have a Canadian station in the format on 88.7 that covers most of the Detroit area, but,they stopped targeting the Detroit side of the border a while back and the station isn't well run or doing well in Canada either. So they basically have the format to themselves there, much different than Chicago.
88.7 in Canada is not set aside for non comms like it is in the USA.
Again if they do flip 95.5 it won't be to Alternative, it would be to something to protect or compliment one of their powerhouse stations like V103 or GCI.
If we do see "ALT" come to Chicago, it won't be on 95.5.
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